Inside the Presidential Portraits: From Washington to Obama

By Oakley Burt, Arts Editor


Throughout the course of American history, each president has had their legacy commemorated with a commissioned portrait – an oil painting on canvas, typically unveiled after leaving office. Not only do these portraits remind us how each president looked, but they also offer a historical lens to the past through a variety of symbols, props and backgrounds. While some presidential portraits are more famous and liked than others, each portrait reveals details about that president and his time holding the highest office in the land. 

The First Portrait and Beginning of a Tradition 

The first full-length painting of founding father George Washington – and first presidential portrait – was commissioned in 1797, in the final year of Washington’s presidency. The portrait was painted by Gilbert Stuart, who chose not to depict Washington as a military leader, but rather as an authoritative leader of a newly free world. In Stuart’s portrait, Washington is standing, dressed in black clothing, holding a sword in his left hand with his right arm outstretched – a book titled “Constitution and Laws of the United States” leans against a table leg.

Further describing the portrait, the New York newspaper Time Piece wrote on February 7, 1798, “A full-length of General Washington (large as life) represented in the position of addressing Congress.  He is surrounded by allegorical emblems of his public life in service to his country, which is highly illustrative of the great and tremendous storms which have frequently prevailed. These storms have abated and the appearance of the rainbow is introduced in the background as a sign.”

Washington’s portrait – the somber backdrop paired with a stiff, dignified pose and stern facial expression – would become the blueprint for every president’s portrait for well over a century. Some of the most striking early presidential portraits include those of Thomas Jefferson, Abraham Lincoln and  Theodore Roosevelt.

Modern Portraits and Symbolic Meaning 

Over the years, many artists commissioned to paint the presidential portraits have gone against the mold and chosen less traditionalistic stylings of the nation’s leaders – opting for brighter colors, softened expressions and casual poses.

One of the first modern expressionist portraits is that of the late President John F. Kennedy. Abstract painter Elaine de Kooning had held several informal sessions with President Kennedy in late 1962 and early 1963 before his death in Palm Beach, Florida. After the assassination, Kooning was so moved by the sessions, creating one of the most famous presidential portraits. Using hues of yellow, aqua and green, Kooning’s portrait saw President Kennedy sitting uncomfortably in a chair, bracing his back – alluding to his back problems that were not known to the American public. “She painted him as she saw him, a true to life moment when he was physically uncomfortable,” Kate Lemay, a historian at the National Portrait Gallery, told TIME. “It’s a true to life moment. I think people just tend to forget that [Presidents] are human, with both physical flaws and character flaws.” 

Looking at symbolism, an intriguing portrait is that of President Bill Clinton painted by artist Nelson Shanks. Unveiled in 2006, Shanks opted for a visually subtle symbolic depiction that spoke volumes. In a 2015 interview with the Philadelphia Inquirer, Shank revealed that a shadow in the painting near the former president was a reference to the infamous blue dress worn by Monica Lewinsky – a former White House intern, whose relationship with Clinton ultimately led to his impeachment. “He and his administration did some very good things, of course,” Shanks told the Philadelphia Inquirer, “but I could never get this Monica thing completely out of mind, and it is subtly incorporated in the painting.” He added, “It is also a bit of a metaphor in that it represents a shadow on the office he held, or on him.”

A recent portrait that blends both modern artistic elements and symbolism is the official one for President Obama, unveiled in 2018. In choosing an artist, President Barack Obama stressed the importance of having an African-American artist commission the painting – selecting Kehinde Wiley for the task. The stunning portrait depicts President Obama sitting in a wooden chair backed by a beautifully colorful, leafy background. Wiley said the background foliage imagery he chose for the portrait was a way of symbolically “charting Obama’s path on Earth.” Wiley included African blue lilies for the former president’s Kenyan heritage; jasmine for Hawaii, where he was born; and chrysanthemums, the official flower of his home state of Chicago. 

Final Thoughts

The tradition of presidential portraits is one that I have admired throughout my studies of American history. Each portrait is unique, expressing the artist’s skills of depicting life and legacy. These fine art portraits are a way to honor each president’s extraordinary life and contribution to American democracy. 

The National Portrait Gallery, located inside the Smithsonian, houses over 1600 presidential portraits in their collection. The portraits can be viewed on their website


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